Selective transacylation reactions on 4-aryl-3,4-dihydropyrimidin-2-ones and nucleosides mediated by novel lipases

Poonam,; Prasad, Ashok K.; Mukherjee, Chandrani; Shakya, Gaurav; Meghwanshi, Gautam K.; Wengel, Jesper; Saxena, Rajendra K.; Parmar, Virinder S.

doi:10.1351/pac200577010237

Pure Appl. Chem., 2005, Vol. 77, No. 1, pp. 237-243

http://dx.doi.org/10.1351/pac200577010237

Selective transacylation reactions on 4-aryl-3,4-dihydropyrimidin-2-ones and nucleosides mediated by novel lipases

Poonam¹, Ashok K. Prasad¹, Chandrani Mukherjee¹, Gaurav Shakya¹, Gautam K. Meghwanshi², Jesper Wengel³, Rajendra K. Saxena² and Virinder S. Parmar¹

¹ Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
² Department of Microbiology, University of Delhi South Campus, Benito Juarez Road, New Delhi 110 021, India
³ Nucleic Acid Center, Department of Chemistry, University of Southern Denmark, Campusvej 55, DK‑5230 Odense M, Denmark

Abstract: Different (±)-4-(3/4-acetoxyaryl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2-ones have been synthesized and subjected to enantioselective deacetylation reactions mediated by different lipases in organic media. Novozyme 435 in tetrahydrofuran:diisopropyl ether was found to be the catalyst of choice for efficient enantioselective deacetylation of dihydropyrimidinones under study. Further, we discovered that lipase isolated from Pseudomonas aeruginosa can be used for selective acylation of secondary hydroxyl groups in nucleosides. This observation can be very useful for selective manipulation of different hydroxyl groups in nucleosides.